diff --git a/src/pretix/control/forms/orders.py b/src/pretix/control/forms/orders.py
index f5be0b529..77625386f 100644
--- a/src/pretix/control/forms/orders.py
+++ b/src/pretix/control/forms/orders.py
@@ -33,6 +33,7 @@
 # distributed on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the
 # License for the specific language governing permissions and limitations under the License.
 
+import os.path
 from datetime import date, datetime, time
 from decimal import Decimal
 
@@ -68,6 +69,7 @@ from pretix.base.services.placeholders import FormPlaceholderMixin
 from pretix.base.services.pricing import get_price
 from pretix.control.forms import SplitDateTimeField
 from pretix.control.forms.widgets import Select2
+from pretix.helpers.hierarkey import clean_filename
 from pretix.helpers.money import change_decimal_field
 
 
@@ -723,6 +725,9 @@ class OrderMailForm(forms.Form):
         help_text=_("Will be ignored if tickets exceed a given size limit to ensure email deliverability."),
         required=False
     )
+    attach_new_order = forms.BooleanField(
+        required=False
+    )
     attach_invoices = forms.ModelMultipleChoiceField(
         label=_("Attach invoices"),
         widget=forms.CheckboxSelectMultiple,
@@ -759,6 +764,12 @@ class OrderMailForm(forms.Form):
         self.fields['attach_invoices'].queryset = order.invoices.all()
         self._set_field_placeholders('message', ['event', 'order'])
         self._set_field_placeholders('subject', ['event', 'order'])
+        if order.event.settings.mail_attachment_new_order:
+            self.fields['attach_new_order'].label = _('Attach {file}').format(
+                file=clean_filename(os.path.basename(order.event.settings.mail_attachment_new_order.name))
+            )
+        else:
+            del self.fields['attach_new_order']
 
 
 class OrderPositionMailForm(OrderMailForm):
diff --git a/src/pretix/control/templates/pretixcontrol/order/sendmail.html b/src/pretix/control/templates/pretixcontrol/order/sendmail.html
index 5681c1cd3..42d3d693c 100644
--- a/src/pretix/control/templates/pretixcontrol/order/sendmail.html
+++ b/src/pretix/control/templates/pretixcontrol/order/sendmail.html
@@ -19,6 +19,9 @@
             {% bootstrap_field form.subject layout='horizontal' %}
             {% bootstrap_field form.message layout='horizontal' %}
             {% bootstrap_field form.attach_tickets layout='horizontal' %}
+            {% if form.attach_new_order %}
+                {% bootstrap_field form.attach_new_order layout='horizontal' %}
+            {% endif %}
             {% if form.attach_invoices %}
                 {% bootstrap_field form.attach_invoices layout='horizontal' %}
             {% endif %}
diff --git a/src/pretix/control/views/orders.py b/src/pretix/control/views/orders.py
index 71a0c998c..cd0327a4f 100644
--- a/src/pretix/control/views/orders.py
+++ b/src/pretix/control/views/orders.py
@@ -2385,6 +2385,9 @@ class OrderSendMail(EventPermissionRequiredMixin, OrderViewMixin, FormView):
                     self.request.user, auto_email=False,
                     attach_tickets=form.cleaned_data.get('attach_tickets', False),
                     invoices=form.cleaned_data.get('attach_invoices', []),
+                    attach_other_files=[a for a in [
+                        self.request.event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
+                    ] if a] if form.cleaned_data.get('attach_new_order', False) else [],
                 )
                 messages.success(self.request,
                                  _('Your message has been queued and will be sent to {}.'.format(order.email)))
@@ -2453,6 +2456,9 @@ class OrderPositionSendMail(OrderSendMail):
                     'pretix.event.order.position.email.custom_sent',
                     self.request.user,
                     attach_tickets=form.cleaned_data.get('attach_tickets', False),
+                    attach_other_files=[a for a in [
+                        self.request.event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
+                    ] if a] if form.cleaned_data.get('attach_new_order', False) else [],
                 )
                 messages.success(self.request,
                                  _('Your message has been queued and will be sent to {}.'.format(position.attendee_email)))